HCID 46238383, compound → HCID 49790728, compound

HRID 526066Notes

Reaction equation

HRID 526066 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[CH:6]=[C:5]2[C:17]([NH:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[O:18]>CN(C=O)C.C(OCC)(=O)C>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:7]1[CH:6]=[C:5]([C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:18])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:2]3[CH:3]=[CH:4][CH:9]=[CH:10][CH:11]=3)[CH:3]=2)[N:8]=1

Participants

4

Reactant 1

HCID 46238383HCID 46238383, compound

Product 1

HCID 49790728HCID 49790728, compoundYield 124.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a sealed tube under argon atmosphere was added 6-bromo-2-(furan-2-yl)-N-(pyridin-3-yl)quinoline-4-carboxamide (0.250 g) in DMF (5 ml), and the vessel was purged with argon under stirring for 5 minutes. After 5 minutes, 2N solution of sodium carbonate in water (3.3 ml) was added and the tube was purged with argon under stirring for 5 minutes. Phenylboronic acid (0.115 g) was then added and the tube was purged with argon under stirring for 15 minutes. Finally, palladium(0)tetrakis triphenylphosphine (0.034 g) was added under argon and the tube was sealed and heated to 90° C. for 16 hours. The completion of the reaction was monitored by TLC using ethyl acetate:hexanes (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (100 ml) and then washed with water (5*100 ml). The ethyl acetate layer was dried over anhydrous sodium sulphate, and the solvent was removed by distillation and the crude product was subjected to purification by silica gel column chromatography, eluting with 1-2% methanol in methylene chloride to provide 0.154 g of 2-(furan-2-yl)-6-phenyl-N-(pyridin-3-yl)quinoline-4-carboxamide (1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.13 (s, 1H), 8.59 (m, 1H), 8.39 (m, 1H), 8.37 (s, 1H), 8.30 (m, 1H), 8.25 (s, 1H), 8.19 (m, 2H), 8.02 (s, 1H), 7.79 (m, 2H), 7.55 (m, 3H), 7.46 (m, 2H), 6.79 (m, 1H); m/z 392.2 (MH+).

Workup

  1. customthe vessel was purged with argon
  2. waitAfter 5 minutes
  3. addition2N solution of sodium carbonate in water (3.3 ml) was added
  4. customthe tube was purged with argon
  5. stirringunder stirring for 5 minutes
  6. additionPhenylboronic acid (0.115 g) was then added
  7. customthe tube was purged with argon
  8. stirringunder stirring for 15 minutes
  9. additionFinally, palladium(0)tetrakis triphenylphosphine (0.034 g) was added under argon
  10. customthe tube was sealed
  11. customAfter completion of the reaction
  12. washwashed with water (5*100 ml)
  13. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  14. customthe solvent was removed by distillation
  15. customthe crude product was subjected to purification by silica gel column chromatography
  16. washeluting with 1-2% methanol in methylene chloride

Sources & evidence

ORD record
ord-fb4ac63d51e9431a88312f2b8ddd893b
Source dataset
uspto-grants-2016_05
Patent number
US09345700B2

Reaction notes

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